The boom in the digital content industry has led to an explosion in the number of creative freelancers, of which the domestic freelance variety shows’ program-director community is a key representative. In the context of local audiovisual content production, this group shows a tendency to pursue high-level projects and manage their personal career portfolios. Drawing on the theory of the Professional Self and using qualitative research methods, the study reveals the process by which freelance program directors strategically address work-linkage issues in their work practices to achieve professional identity and self-positioning: the individual practitioner's differentiated practices of freelancing are aggregated into a collective professional imaginary through the act of self-employment, and then re-identified and re-positioned collectively through the portfolios, which is perceived to be the more visible reputational capital. The discussion of freelance program directors' transition from differentiated practice to portfolio dependent processes highlights the importance of dynamic, processual, and endogenous situations in the construction of the professional selves, and the study clarifies the central role of the Situational Selves in this regard for contemporary creative media freelancers. By placing the Professional Self theory in the larger context of the Social Self view, it enhances the explanatory power of this theory for emerging occupational phenomena and problems in the current digital age.